The present invention relates to a novel compound suitable for use as a dye for a filter, a color conversion filter, a dye for a photographic material, a sensitizing dye, a dye for pulp dyeing, a laser dye, a fluorescent medicine for a medical diagnosis, a material for an organic luminescence element, etc., and an organic luminescence element using the same.
Prospects of an organic luminescence element in which organic materials are used are promising as a solid luminescent type inexpensive and large area full color display element and development has been tried variously. In general, an organic luminescence element comprises a luminescent layer and a pair of counter electrodes with the luminescent layer between. When electric field is impressed between both electrodes, electrons are injected from the cathode and positive holes are injected from the anode, and the electrons and positive holes are recombined in the luminescent layer. A phenomenon of emitting energy as light when energy level is returned from conduction band to valence band is luminescence.
Organic luminescence elements so far been used require high driving voltage and luminance and luminescent efficacy are low, but various techniques for improving these points are reported in recent years. For example, there is known a luminescence element comprising organic thin layers formed by vapor deposition of organic compounds (Applied Physics Letters, Vol. 51, p. 913 (1987)). This organic luminescence element comprises the lamination structure of an electron-transporting material and a positive hole-transporting material, and the luminescent characteristics have been remarkably improved as compared with conventionally used single layer type elements.
Al complex of 8-quinolinol (Alq) is used as a luminescent material in the above element and a luminescent color is green, but when taking into consideration the utilization as a full color display and a light source, it is necessary to get three primary colors or a white color in practical use. As the improved element thereof, an element to which a fluorescent dye is doped is reported (Journal of Applied Physics, Vol. 65, p. 3610 (1989)). According to the above report, reddish orange luminescence is obtained by doping 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4-H-pyran (DCM), but this element is impracticable as color purity is low and durability is low. Similarly, although various organic luminescence elements which emit light in longer wavelength range than green have been developed by doping fluorescent materials, any of these elements has serious drawbacks that color purity is low as red luminescence and sufficient luminance cannot be obtained. Further, there is another problem that organic luminescence elements in which conventional red fluorescent dyes are used exhibit low durability.
Further, conventionally used elements which have excellent color purity and high luminescent efficacy are those having been doped with a small amount of a fluorescent dye in an electric charge-transporting material. Such elements have drawbacks that characteristics of elements are difficult to be reproduced from the manufacturing technique and the durability of the dye is low, as a result, the luminance is reduced or the color changes after being used for a long period of time. To cope with these problems, development of a material which functions as an electric charge-transporting material and a luminescent material in one has been desired. However, with materials so far been developed, when a fluorescent dye is used in high concentration as an electric-transporting material, emission with high luminance is difficult as quenching due to concentration occurs.
On the other hand, organic luminescence elements which have realized high luminance emission are laminated elements formed by vacuum deposition of organic materials, but from the viewpoint of simplification of producing step, processability, and realization of large area elements, it is desired to produce elements by a coating system. However, elements produced by a coating system so far been used are inferior to those produced by a vapor deposition system in luminance and luminescent efficacy, therefore, high luminance and luminescence with high efficacy have been left as problems to be solved.
Further, in recent years, various materials having fluorescence have been used in a dye for a filter, a color conversion filter, a dye for a photographic material, a sensitizing dye, a dye for pulp dyeing, a laser dye, a fluorescent medicine for a medical diagnosis, a material for an organic luminescence element, etc., and demand for such materials has been increased. However, red fluorescent dyes having high fluorescent strength and high color purity are less, therefore, the development of a novel material has been desired.
A first object of the present invention is to provide a red fluorescent compound having high color purity and to provide an organic luminescence element using the same.
A second object of the present invention is to provide a material for an organic luminescence element capable of emission of high luminance and high efficacy by low voltage-driving and excellent in stability by repeating use, and to provide an organic luminescence element using the same.
A third object of the present invention is to provide a material emitting a red color necessary to realize white luminescence and to provide an organic luminescence element using the same.
A fourth object of the present invention is to provide a material for an organic luminescence element capable of emission of high luminance and high efficacy even when produced by a coating system and to provide an organic luminescence element using the same.
A fifth object of the present invention is to provide a compound having high fluorescent strength in a reddish orange to near infrared region.
The above objects of the present invention have been achieved by the following means.
(1A) A methine compound represented by the following formula (I): 
wherein R1, R2, R3, R4 and R5 each represents a hydrogen atom or a substituent; X represents an oxygen atom, a sulfur atom, or Nxe2x80x94R6; Z represents xe2x80x94NR7R8, or xe2x80x94OG; R6, R7 and R8 each represents a hydrogen atom or a substituent; G represents a hydrogen atom, a cation or a substituent; L1, L2 and L3 each represents a substituted or unsubstituted methine group; n represents 1 or 2; and W represents an electron attractive group (electron withdrawing group).
(2A) A methine compound represented by the following formula (I-a): 
wherein R1, R2, R3, R4, R5, R7 and R8 each represents a hydrogen atom or a substituent; L1, L2 and L3 each represents a substituted or unsubstituted methine group; n represents 1 or 2; and W represents an electron attractive group.
(3A) A methine compound represented by the following formula (I-b): 
wherein R1, R2, R3, R4, R5, R7, R8, Rb1, Rb2, Rb3 and Rb4 each represents a hydrogen atom or a substituent; and Wb1 and Wb2 each represents an electron attractive group.
(4A) A methine compound represented by the following formula (I-c): 
wherein R1, R2, R3, R4, R5, R7, R8, Rb1, Rb2, Rb3 and Rb4 each represents a hydrogen atom or a substituent.
(5A) A methine compound represented by the following formula (I-d): 
wherein R1, R2, R3, R4, R5, R7, R8, Rb1, Rb2, Rb3 and Rb4 each represents a hydrogen atom or a substituent; and Q represents an atomic group necessary for forming a 5- or 6-membered ring.
(6A) A methine compound represented by the following formula (I-e): 
wherein R1, R2, R3, R4, R5, R7, R8, Rb1, Rb2, Rb3 and Rb4 each represents a hydrogen atom or a substituent; and Qe represents an atomic group necessary for forming a 5- or 6-membered ring.
(7A) A material for an organic luminescence element which is represented by formula (I), (I-a), (I-b), (I-c), (I-d) or (I-e) as described in the above item (1A), (2A), (3A), (4A), (5A) or (6A).
(8A) An organic luminescence element comprising a pair of electrodes having formed therebetween a luminescent layer or a plurality of organic compound thin layers including a luminescent layer, wherein at least one layer is a layer containing a methine compound represented by formula (I), (I-a), (I-b), (I-c), (I-d) or (I-e) as described in the above item (1A), (2A), (3A), (4A), (5A) or (6A).
(9A) An organic luminescence element comprising a pair of electrodes having formed therebetween a luminescent layer or a plurality of organic compound thin layers including a luminescent layer, wherein at least one layer is a layer having dispersed in a polymer a methine compound represented by formula (I), (I-a), (I-b), (I-c), (I-d) or (I-e) as described in the above item (1A), (2A), (3A), (4A), (5A) or (6A).
(1B) A material for an organic luminescence element which is a compound represented by the following formula (II): 
wherein R1, R2, R3, R4, R5, R6, R7, R8 and R9 each represents a hydrogen atom or a substituent; X represents an oxygen atom, a sulfur atom, or N-R10 (wherein R10 represents a hydrogen atom or a substituent); Z, represents an atomic group necessary for forming a 5- or 6-membered ring; L1 and L2 each represents a substituted or unsubstituted methine group; and n represents 1 or 2.
(2B) A material for an organic luminescence element which is a compound represented by the following formula (III): 
wherein R1, R2, R3, R4, R5, R6, R7, R8 and R9 each represents a hydrogen atom or a substituent; Z2 represents an atomic group necessary for forming a 5- or 6-membered ring; L1 and L2 each represents a substituted or unsubstituted methine group; and n represents 1 or 2.
(3B) A compound represented by the following formula (IV): 
wherein R1, R2, R3, R4, R5, R6, R7 and R8 each represents a hydrogen atom or a substituent; R31 represents an alkyl group having 2 or more carbon atoms, or an aryl group having 6 or more carbon atoms; Z2 represents an atomic group necessary for forming a 5- or 6-membered ring; L1 and L2 each represents a substituted or unsubstituted methine group; and n represents 1 or 2.
(4B) A material for an organic luminescence element which is a compound represented by the following formula (IV): 
wherein R1, R2, R3, R4, R5, R6, R7 and R8 each represents a hydrogen atom or a substituent; R31 represents an alkyl group having 2 or more carbon atoms, or an aryl group having 6 or more carbon atoms; Z2 represents an atomic group necessary for forming a 5- or 6-membered ring; L1 and L2 each represents a substituted or unsubstituted methine group; and n represents 1 or 2.
(5B) A compound represented by the following formula (IV-a): 
wherein R1, R2, R3, R4, R5, R6, R7, R8, R41, R42, R43 and R44 each represents a hydrogen atom or a substituent; R31 represents an alkyl group having 2 or more carbon atoms, or an aryl group having 6 or more carbon atoms; L1 and L2 each represents a substituted or unsubstituted methine group; and n represents 1 or 2.
(6B) A material for an organic luminescence element which is a compound represented by the following formula (IV-a): 
wherein R1, R2, R3, R4, R5, R6, R7, R8, R41, R42, R43 and R44 each represents a hydrogen atom or a substituent; R31 represents an alkyl group having 2 or more carbon atoms, or an aryl group having 6 or more carbon atoms; L1 and L2 each represents a substituted or unsubstituted methine group; and n represents 1 or 2.
(7B) A compound represented by the following formula (V): 
wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R51 and R52 each represents a hydrogen atom or a substituent; L1 and L2 each represents a substituted or unsubstituted methine group; and n represents 1 or 2.
(8B) A material for an organic luminescence element which is a compound represented by the following formula (V): 
wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R51 and R52 each represents a hydrogen atom or a substituent; L1 and L2 each represents a substituted or unsubstituted methine group; and n represents 1 or 2.
(9B) An organic luminescence element comprising a pair of electrodes having formed therebetween a luminescent layer or a plurality of organic compound thin layers including a luminescent layer, wherein at least one layer is a layer containing a compound represented by formula (II), (III), (IV), (IV-a) or (V) described in the above item (1B), (2B), (4B), (6B) or (8B).
(10B) An organic luminescence element comprising a pair of electrodes having formed therebetween a luminescent layer or a plurality of organic compound thin layers including a luminescent layer, wherein at least one layer is a layer having dispersed in a polymer a compound represented by formula (II), (III), (IV), (IV-a) or (V) described in the above item (1B), (2B), (4B), (6B) or (8B).
(1C) A methine compound represented by the following formula (VI): 
wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R each represents a hydrogen atom or a substituent; A represents a heterocyclic ring containing an aromatic ring; X represents an oxygen atom, a sulfur atom, or Nxe2x80x94R10 (wherein R10 represents a hydrogen atom or a substituent); L1 and L2 each represents a substituted or unsubstituted methine group; and n represents 1 or 2.
(2C) A material or an organic luminescence element represented by formula (VI) described in item (1C).
(3C) An organic luminescence element comprising a pair of electrodes having formed therebetween a luminescent layer or a plurality of organic compound thin layers including a luminescent layer, wherein at least one layer is a layer containing a methine compound described in item (1C).
(4C) An organic luminescence element comprising a pair of electrodes having formed therebetween a luminescent layer or a plurality of organic compound thin layers including a luminescent layer, wherein at least one layer is a layer having dispersed in a polymer a methine compound described in item (1C).
The compound represented by formula (I) of the present invention is described in detail below.
R1, R2, R3, R4 and R5 each represents a hydrogen atom or a substituent. Examples of the substituents represented by R1, R2, R3, R4 and R5 include an alkyl group (preferably an alkyl group having from 1 to 20, more preferably from 1 to 12, and particularly preferably from 1 to 8, carbon atoms, e.g., methyl, ethyl, isopropyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl), an alkenyl group (preferably an alkenyl group having from 2 to 20, more preferably from 2 to 12, and particularly preferably from 2 to 8, carbon atoms, e.g., vinyl allyl, 2-butenyl, 3-pentenyl), an alkynyl group (preferably an alkynyl group having from 2 to 20, more preferably from 2 to 12, and particularly preferably from 2 to 8, carbon atoms, e.g., propargyl, 3-pentynyl), an aryl group (preferably an aryl group having from 6 to 30, more preferably from 6 to 20, and particularly preferably from 6 to 12, carbon atoms, e.g., phenyl, p-methylphenyl, 2,4, 6-trimethylphenyl, naphthyl), an amino group (preferably an amino group having from 0 to 20, more preferably from 0 to 10, and particularly preferably from 0 to 6, carbon atoms, e.g., amino, methylamino, dimethylamino, diethylamino, benzylamino), an alkoxyl group (preferably an alkoxyl group having from 1 to 20, more preferably from 1 to 12, and particularly preferably from 1 to 8, carbon atoms, e.g., methoxy, ethoxy, butoxy), an aryloxy group (preferably an aryloxy group having from 6 to 20, more preferably from 6 to 16, and particularly preferably from 6 to 12, carbon atoms, e.g., phenyloxy, 2-naphthyloxy), an acyl group (preferably an acyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., acetyl, benzoyl, formyl, pivaloyl), an alkoxycarbonyl group (preferably an alkoxycarbonyl group having from 2 to 20, more preferably from 2 to 16, and particularly preferably from 2 to 12, carbon atoms, e.g., methoxycarbonyl, ethoxycarbonyl), an aryloxycarbonyl group (preferably an aryloxycarbonyl group having from 7 to 20, more preferably from 7 to 16, and particularly preferably from 7 to 10, carbon atoms, e.g., phenyloxycarbonyl), an acyloxy group (preferably an acyloxy group having from 2 to 20, more preferably from 2 to 16, and particularly preferably from 2 to 10, carbon atoms, e.g., acetoxy, benzoyloxy), an acylamino group (preferably an acylamino group having from 2 to 20, more preferably from 2 to 16, and particularly preferably from 2 to 10, carbon atoms, e.g., acetylamino, benzoylamino), an alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having from 2 to 20, more preferably from 2 to 16, and particularly preferably from 2 to 12, carbon atoms, e.g., methoxycarbonylamino), an aryloxycarbonylamino group (preferably an aryloxycarbonylamino group having from 7 to 20, more preferably from 7 to 16, and particularly preferably from 7 to 12, carbon atoms, e.g., phenyloxycarbonylamino), a sulfonylamino group (preferably a sulfonylamino group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., methanesulfonylamino, benzenesulfonylamino), a sulfamoyl group (preferably a sulfamoyl group having from 0 to 20, more preferably from 0 to 16, and particularly preferably from 0 to 12, carbon atoms, e.g., sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl), a carbamoyl group(preferably a carbamoyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl), an alkylthio group (preferably an alkylthio group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., methylthio, ethylthio), an arylthio group (preferably an arylthio group having from 6 to 20, more preferably from 6 to 16, and particularly preferably from 6 to 12, carbon atoms, e.g., phenylthio), a sulfonyl group (preferably a sulfonyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., mesyl, tosyl), a sulfinyl group (preferably a sulfinyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., methanesulfinyl, benzenesulfinyl), a ureido group (preferably a ureido group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., ureido, methylureido, phenylureido), a phosphoric acid amido group (preferably a phosphoric acid amido group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., diethylphosphoric acid amido, phenylphosphoric acid amido), a hydroxyl group, a mercapto group, a halogen atom (e.g., fluorine, chlorine, bromine, iodine), a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, an imino group, and a heterocyclic group (preferably a heterocyclic group having from 1 to 20, and more preferably from 1 to 12, carbon atoms; as hetero atoms, e.g., nitrogen, oxygen, sulfur, and specifically, e.g., imidazolyl, pyridyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzothiazolyl can be exemplified). These substituents may further be substituted. When there are two or more substituents, they may be the same or different. Substituents may be linked together to form a ring, if possible.
Preferred examples of the substituents include an alkyl group, an alkenyl group, an aralkyl group, an aryl group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, a cyano group, a halogen atom, a hydroxyl group, and a heterocyclic group, more preferred examples include an alkyl group, an aralkyl group, an aryl group, an acyl group, an alkoxycarbonyl group, a carbonylamino group, a sulfonylamino group, a cyano group, a halogen atom, and a heterocyclic group, and still more preferred examples include an alkyl group, an aryl group, an alkoxycarbonyl group, a cyano group, and an azole group.
R1 preferably represents a hydrogen atom, an alkoxycarbonyl group, a cyano group, or an azole group, and more preferably represents a hydrogen atom.
R2 preferably represents a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a lower alkyl group, and particularly preferably a hydrogen atom or a methyl group.
R3 preferably represents a hydrogen atom, an alkyl group, or a halogen atom, and more preferably a hydrogen atom.
R4 and R5 each preferably represents a hydrogen atom, an alkyl group, or an alkylene group, more preferably a hydrogen atom, a lower alkyl group (having from 1 to 4 carbon atoms), or an alkylene group, and still more preferably a hydrogen atom or an alkylene group which is formed by linking with R7 or R8 to form a 6-membered ring as described later.
X represents an oxygen atom, a sulfur atom, or Nxe2x80x94R6, wherein R6 represents a hydrogen atom or a substituent. Examples of the substituents represented by R6 include, for example, an alkyl group (preferably an alkyl group having from 1 to 20, more preferably from 1 to 12, and particularly preferably from 1 to 8, carbon atoms, e.g., methyl, ethyl, isopropyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl), an alkenyl group (preferably an alkenyl group having from 2 to 20, more preferably from 2 to 12, and particularly preferably from 2 to 8, carbon atoms, e.g., vinyl, allyl, 2-butenyl, 3-pentenyl), an alkynyl group (preferably an alkynyl group having from 2 to 20, more preferably from 2 to 12, and particularly preferably from 2 to 8, carbon atoms, e.g., propargyl, 3-pentynyl), an aryl group (preferably an aryl group having from 6 to 30, more preferably from 6 to 20, and particularly preferably from 6 to 12, carbon atoms, e.g., phenyl, p-methylphenyl, naphthyl), an acyl group (preferably an acyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., acetyl, benzoyl, formyl, pivaloyl), an alkoxycarbonyl group (preferably an alkoxycarbonyl group having from 2 to 20, more preferably from 2 to 16, and particularly preferably from 2 to 12, carbon atoms, e.g., methoxycarbonyl, ethoxycarbonyl), an aryloxycarbonyl group (preferably an aryloxycarbonyl group having from 7 to 20, more preferably from 7 to 16, and particularly preferably from 7 to 10, carbon atoms, e.g., phenyloxycarbonyl), a sulfamoyl group (preferably a sulfamoyl group having from 0 to 20, more preferably from 0 to 16, and particularly preferably from 0 to 12, carbon atoms, e.g., sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl), a carbamoyl group(preferably a carbamoyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl), a sulfonyl group (preferably a sulfonyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., mesyl, tosyl), a sulfinyl group (preferably a sulfinyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., methanesulfinyl, benzenesulfinyl), and a heterocyclic group (preferably a heterocyclic group having from 1 to 20, and more preferably from 1 to 12, carbon atoms; as hetero atoms, e.g., nitrogen, oxygen, sulfur, and specifically, e.g., imidazolyl, pyridyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzothiazolyl can be exemplified). These substituents may further be substituted. When there are two or more substituents, they may be the same or different. Substituents may be linked together to form a ring, if possible.
Preferred examples of the substituents represented by R6 include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, and a heterocyclic group, more preferred are an alkyl group, an aryl group, and an aromatic heterocyclic group, and still more preferred examples include an alkyl group and an aryl group.
X preferably represents an oxygen atom or Nxe2x80x94R6, and more preferably an oxygen atom.
Z represents xe2x80x94NR7R8, or xe2x80x94OG, wherein R7 and R8 each represents a hydrogen atom or a substituent, G represents a hydrogen atom, a cation or a substituent.
As the substituents represented by R7 and R8, those described in R6 can be applied. R7 and R8 each preferably represents an alkyl group, an alkylene group, an aryl group, or a heterocyclic group, more preferably an alkyl group, an alkylene group, an aryl group, or an aromatic heterocyclic group, and still more preferably an alkyl group, an aryl group, or an alkylene group formed by linking R4 with R7 and R5 with R8 to form a 6-membered ring.
R7 and R8 each preferably represents a hydrogen atom, an alkyl group, an alkylene group, an aryl group, or an aromatic heterocyclic group, and more preferably a hydrogen atom, an alkyl group, an alkylene group which is formed by linking R4 with R7 and R5 with R8 to form a 6-membered ring, or an aryl group, and particularly preferably a lower alkyl group (having from 1 to 4 carbon atoms), an alkylene group formed by linking R4 with R7 and R5 with R8 to form a 6-membered ring, or an aryl group.
The cation represented by G is not particularly limited and, for example, a metal cation (e.g., a lithium ion, a sodium ion, a potassium ion, a cesium ion, a magnesium ion, a calcium ion, an aluminum ion, an europium ion), and an ammonium ion (preferably having from 0 to 30, more preferably from 0 to 20, and still more preferably from 0 to 10, carbon atoms, e.g., a tetrabutylammonium ion) can be exemplified. These metal cations may have ligands.
As the substituents represented by G, those described in R6 can be cited, preferably an alkyl group (preferably an alkyl group having from 1 to 30, more preferably from 1 to 20, and still more preferably from 1 to 10, carbon atoms, e.g., methyl, ethyl, n-propyl, isopropyl, methoxyethoxymethyl), or an aryl group (preferably an aryl group having from 6 to 30, more preferably from 6 to 20, and still more preferably from 6 to 10, carbon atoms, e.g., phenyl, p-methoxyphenyl), and more preferably an alkyl group.
G preferably represents a hydrogen atom, an alkyl group, an aryl group, an alkali metal ion, an alkaline earth metal ion, an aluminum ion, a zinc ion, an europium ion, or a quaternary ammonium ion, more preferably a hydrogen atom, an alkyl group, or an aryl group, and still more preferably a hydrogen atom.
Z preferably represents xe2x80x94NR7R8.
L1, L2 and L3 each represents a substituted or unsubstituted methine group. L1 and L2 may respectively form 4- to 6-membered rings via the substituent of the substituted methine group, or L1 and L2, L2 and L3, and L3 and W may be respectively linked to each other to form 4- to 6-membered rings.
As the substituents of the substituted methine group, e.g., those exemplified as the substituents for R1 to R5 can be applied, preferably an alkyl group, an aryl group, an aralkyl group, an alkoxyl group, an aryloxy group, an alkylthio group, an arylthio group, a cyano group, or a halogen atom, more preferably an alkyl group or an alkoxyl group, and still more preferably a lower alkyl group (preferably having from 1 to 4 carbon atoms).
L1, L2 and L3 each preferably represents an unsubstituted methine group, an alkyl-substituted methine group, or an alkoxyl-substituted methine group.
n represents 1 or 2, preferably 2.
W represents an electron attractive group, e.g., a cyano group, a carbonyl group, a thiocarbonyl group, an aryl group (e.g., phenyl, naphthyl), an aromatic heterocyclic group (e.g., pyridyl, quinolyl, furyl, thienyl, oxazolyl, thiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzoselenazolyl, pyrimidyl), a sulfonyl group, a carbamoyl group, a sulfamoyl group can be exemplified.
Preferred examples of the electron attractive groups represented by W are a cyano group, a carbonyl group, a sulfonyl group, and an aromatic heterocyclic group, and more preferred are a cyano group and a carbonyl group.
The compound represented by formula (I) is preferably represented by formula (I-a): 
wherein R1, R2, R3, R4, R5, R7, R8, L1, L2, L3, n and W each has the same meaning as defined in formula (I), and the preferred range is also the same.
The compound represented by formula (I) is more preferably represented by formula (I-b): 
wherein R1, R2, R3, R4, R5, R7 and R8 each has the same meaning as defined in formula (I), and the preferred range is also the same. Wb1 and Wb2 each has the same meaning as W in formula (I), and the preferred range is also the same. Rb1, Rb2, Rb3 and Rb4 each represents a hydrogen atom or a substituent. As the substituents represented by Rb1, Rb2, Rb3 and Rb4, e.g., those exemplified as the substituents for R1 to R5 in formula (I) can be applied. Rb1 preferably represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group, and more preferably an alkyl group (preferably an alkyl group having from 1 to 20, more preferably from 1 to 16 carbon atoms, still more preferably from 1 to 12, carbon atoms, and particularly preferably a methyl group or a tert-butyl group), or an aryl group (preferably an aryl group having from 6 to 30 carbon atoms, more preferably a phenyl group having from 6 to 30 carbon atoms and substituted with an alkyl group at the opposition, still more preferably a 2,6-dialkyl-substituted phenyl group, and particularly preferably a 2,6-dimethyl-substituted phenyl group). Rb1 particularly preferably represents a methyl group, a tert-butyl group or a 2,4,6-trimethylphenyl group, and most preferably a tert-butyl group. Rb2, Rb3 and Rb4 each preferably represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group, more preferably a hydrogen atom, or a lower alkyl group, and particularly preferably a hydrogen atom. Rb1 and Rb2 may be linked to each other to form a 6-membered ring.
The compound represented by formula (I) is still more preferably represented by formula (I-c) or (I-d): 
wherein R1, R2, R3, R4, R5, R7 and R8 each has the same meaning as defined in formula (I), and the preferred range is also the same. Rb1, Rb2, Rb3 and Rb4 each has the same meaning as defined in formula (I-b), and the preferred range is also the same; 
wherein R1, R2, R3, R4, R5, R7 and R8 each has the same meaning as defined in formula (I), and the preferred range is also the same. Rb1, Rb2, Rb3 and Rb4 each has the same meaning as defined in formula (I-b), and the preferred range is also the same. Q represents an atomic group necessary for forming a 5- or 6-membered ring. Specific examples of the 5- or 6-membered rings formed by Q include the following:
(a) A 1,3-dicarbonyl nucleus: e.g., 1,3-cyclopentanedione, 1,3-indanedione, 1,3-cyclohexanedione, 5,5-dimethyl-1,3-cyclohexanedione, 1,3-dioxane-4,6-dione, etc.
(b) A pyrazolinone nucleus: e.g., 1-phenyl-2-pyrazolin-5-one, 3-methyl-1-phenyl-2-pyrazolin-5-one, 1-(2-benzothiazolyl)-3-methyl-2-pyrazolin-5-one, etc.
(c) An isooxazolinone nucleus: e.g., 3-phenyl-2-isooxazolin-5-one, 3-methyl-2-isooxazolin-5-one, etc.
(d) An oxyindole nucleus: e.g., 1-alkyl-2,3-dihydro-2-oxyindole, etc.
(e) A 2,4,6-triketohexahydropyrimidine nucleus: e.g., barbituric acid or 2-thiobarbituric acid and derivatives thereof, and as derivatives, e.g., 1-alkyl form such as 1-methyl, 1-ethyl; 1,3-dialkyl form such as 1,3-dimethyl, 1,3-diethyl, 1,3-dibutyl; 1,3-diaryl form such as 1,3-diphenyl, 1,3-di(p-chlorophenyl), 1,3-di(p-ethoxycarbonylphenyl); 1-alkyl-1-aryl form such as 1-ethyl-3-phenyl; and 1,3-di-heterocyclic group substitution product such as 1,3-di(2-pyridyl) can be exemplified.
(f) A 2-thio-2,4-thiazolidinedione nucleus: e.g., rhodanine and derivatives thereof, and as derivatives, e.g., 3-alkylrhodanine such as 3-methylrhodanine, 3-ethylrhodanine, 3-allylrhodanine; 3-arylrhodanine such as 3-phenylrhodanine; and 3-heterocyclic group-substituted rhodanine such as 3-(2-pyridyl)rhodanine can be exemplified.
(g) A 2-thio-2,4-oxazolidinedione (2-thio-2,4-(3H,5H)-oxazoledione) nucleus: e.g., 3-ethyl-2-thio-2,4-oxazolidinedione, etc.
(h) A thianaphthenone nucleus: e.g., 3-(2H)-thianaphthenone-1,1-dioxide, etc.
(i) A 2-thio-2,5-thiazolidinedione nucleus: e.g., 3-ethyl-2-thio-2,5-thiazolidinedione, etc.
(j) A 2,4-thiazolidinedione nucleus: e.g., 2,4-thiazolidinedione, 3-ethyl-2,4-thiazolidinedione, 3-phenyl-2,4-thiazolidinedione, etc.
(k) A thiazolin-4-one nucleus: e.g., 4-thiazolinone, 2-ethyl-4-thiazolinone, etc.
(l) A 4-thiazolidinone nucleus: e.g., 2-ethylmercapto-5-thiazolin-4-one, 2-alkylphenylamino-5-thiazolin-4-one, etc.
(m) A 2,4-imidazolidinedione (hydantoin) nucleus: e.g., 2,4-imidazolidinedione, 3-ethyl-2,4-imidazolidinedione, etc.
(n) A 2-thio-2,4-imidazolidinedione (2-thiohydantoin) nucleus: e.g., 2-thio-2,4-imidazolidinedione, 3-ethyl-2-thio-2,4-imidazolidinedione, etc.
(o) An imidazolin-5-one nucleus: e.g., 2-propylmercapto-2-imidazolin-5-one, etc.
(p) A 3,5-pyrazolidinedione nucleus: e.g., 1,2-diphenyl-3,5-pyrazolidinedione, 1,2-dimethyl-3,5-pyrazolidinedione, etc.
Preferred examples of the rings formed by Q include a 1,3-dicarbonyl nucleus, a pyrazolinone nucleus, a 2,4,6-triketohexahydropyrimidine nucleus (including a thioketone form), a 2-thio-2,4-thiazolidinedione nucleus, a 2-thio-2,4-oxazolidinedione nucleus, a 2-thio-2,5-thiazolidinedione nucleus, a 2,4-thiazolidinedione nucleus, a 2,4-imidazolidinedione nucleus, a 2-thio-2,4-imidazolidinedione nucleus, a 2-imidazolin-5-one nucleus, and a 3,5-pyrazolidinedione nucleus, more preferred are a 1,3-dicarbonyl nucleus, a 2,4,6-triketohexahydropyrimidine nucleus (including a thioketone form), and a 3,5-pyrazolidinedione nucleus, still more preferred are a cyclic 1,3-dicarbonyl nucleus, a barbituric acid derivative, a 2-thiobarbituric acid derivative, and a 3,5-pyrazolidinedione nucleus, particularly preferred are 1,3-indanedione and 1,2-diphenyl-3,5-pyrazolidinedione, and most preferred is 1,3-indanedione.
The compound represented by formula (I-d) is more preferably represented by formula (I-e): 
wherein R1, R2, R3, R4, R5, R7 and R8 each has the same meaning as defined in formula (I), and the preferred range is also the same. Rb1, Rb2, Rb3 and Rb4 each has the same meaning as defined in formula (I-b), and the preferred range is also the same. Qe represents an atomic group necessary for forming a 5- or 6-membered ring. Qe represents an atomic group necessary for forming a 5- or 6-membered ring, as the 5- or 6-membered rings formed by Qe, e.g., among the rings formed by Q in formula (I-d), those having 1,3-dicarbonyl structure in the ring, e.g., 1,3-cyclopentanedione, 1,3-cyclohexanedione, and 1,3-indanedione can be exemplified, and preferred is 1,3-indanedione.
The compound represented by formula (I) may be a low molecular weight compound, may be a high molecular weight compound the polymer main chain of which is connected with the residue represented by formula (I) (preferably having a weight average molecular weight of from 1,000 to 5,000,000, more preferably from 5,000 to 2,000,000, and still more preferably from 10,000 to 1,000,000, calculated in terms of polystyrene), or may be a high molecular weight compound whose main chain has the skeleton of formula (I) (preferably having a weight average molecular weight of from 1,000 to 5,000,000, more preferably from 5,000 to 2,000,000, and still more preferably from 10,000 to 1,000,000, calculated in terms of polystyrene). The high molecular weight compound may be a homopolymer or a copolymer with other monomers.
The compound represented by formula (I) is preferably a low molecular weight compound. Further, formula (I) is conveniently represented as an extreme structural formula but the compound may be a tautomer. When there exists a geometrical isomer, the compound may be either one.
Specific examples of the compound represented by formula (I) are shown below but the present invention is not limited thereto. 
Weight average molecular weight: 13,000 (calculated in terms of polystyrene) 
Weight average molecular weight: 11,800 (calculated in terms of polystyrene)
m/n=1/100 (by weight) 
Weight average molecular weight: 21,000 (calculated in terms of polystyrene)
m/n=1/98 (by weight)
The above-described compounds may be tautomers thereof.
The compound represented by formula (I) can be synthesized according to various synthesis methods. For example, a method of converting the carbonyl group of a coumarin derivative to a thiocarbonyl group and reacting it with an activated methylene compound can be applied.
The compound represented by formula (II) of the present invention is described in detail below.
R1 R2, R3, R4, R5, R6, R7, R8 and R9 each represents a hydrogen atom or a substituent. Examples of the substituents represented by R1, R2, R3, R4, R5, R6, R7, R8 and R9 include an alkyl group (preferably an alkyl group having from 1 to 20, more preferably from 1 to 12, and particularly preferably from 1 to 8, carbon atoms, e.g., methyl, ethyl, isopropyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl), an alkenyl group (preferably an alkenyl group having from 2 to 20, more preferably from 2 to 12, and particularly preferably from 2 to 8, carbon atoms, e.g., vinyl allyl, 2-butenyl, 3-pentenyl), an alkynyl group (preferably an alkynyl group having from 2 to 20, more preferably from 2 to 12, and particularly preferably from 2 to 8, carbon atoms, e. g., propargyl, 3-pentynyl), an aryl group (preferably an aryl group having from 6 to 30, more preferably from 6 to 20, and particularly preferably from 6 to 12, carbon atoms, e.g., phenyl, p-methylphenyl, 2,4,6-trimethylphenyl, naphthyl), an amino group (preferably an amino group having from 0 to 20, more preferably from 0 to 10, and particularly preferably from 0 to 6, carbon atoms, e.g., amino, methylamino, dimethylamino, diethylamino, benzylamino), an alkoxyl group (preferably an alkoxyl group having from 1 to 20, more preferably from 1 to 12, and particularly preferably from 1 to 8, carbon atoms, e.g., methoxy, ethoxy, butoxy), an aryloxy group (preferably an aryloxy group having from 6 to 20, more preferably from 6 to 16, and particularly preferably from 6 to 12, carbon atoms, e.g., phenyloxy, 2-naphthyloxy), an acyl group (preferably an acyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., acetyl, benzoyl, formyl, pivaloyl), an alkoxycarbonyl group (preferably an alkoxycarbonyl group having from 2 to 20, more preferably from 2 to 16, and particularly preferably from 2 to 12, carbon atoms, e.g., methoxycarbonyl, ethoxycarbonyl), an aryloxycarbonyl group (preferably an aryloxycarbonyl group having from 7 to 20, more preferably from 7 to 16, and particularly preferably from 7 to 10, carbon atoms, e.g., phenyloxycarbonyl), an acyloxy group (preferably an acyloxy group having from 2 to 20, more preferably from 2 to 16, and particularly preferably from 2 to 10, carbon atoms, e.g., acetoxy, benzoyloxy), an acylamino group (preferably an acylamino group having from 2 to 20, more preferably from 2 to 16, and particularly preferably from 2 to 10, carbon atoms, e.g., acetylamino, benzoylamino), an alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having from 2 to 20, more preferably from 2 to 16, and particularly preferably from 2 to 12, carbon atoms, e.g., methoxycarbonylamino), an aryloxycarbonylamino group (preferably an aryloxycarbonylamino group having from 7 to 20, more preferably from 7 to 16, and particularly preferably from 7 to 12, carbon atoms, e.g., phenyloxycarbonylamino), a sulfonylamino group (preferably a sulfonylamino group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., methanesulfonylamino, benzenesulfonylamino), a sulfamoyl group (preferably a sulfamoyl group having from 0 to 20, more preferably from 0 to 16, and particularly preferably from 0 to 12, carbon atoms, e.g., sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl), a carbamoyl group (preferably a carbamoyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl), an alkylthio group (preferably an alkylthio group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., methylthio, ethylthio), an arylthio group (preferably an arylthio group having from 6 to 20, more preferably from 6 to 16, and particularly preferably from 6 to 12, carbon atoms, e.g., phenylthio), a sulfonyl group (preferably a sulfonyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., mesyl, tosyl), a sulfinyl group (preferably a sulfinyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., methanesulfinyl, benzenesulfinyl), a ureido group (preferably a ureido group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., ureido, methylureido, phenylureido), a phosphoric acid amido group (preferably a phosphoric acid amido group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., diethylphosphoric acid amido, phenylphosphoric acid amido), a hydroxyl group, a mercapto group, a halogen atom (e.g., fluorine, chlorine, bromine, iodine), a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, an imino group, and a heterocyclic group (preferably a heterocyclic group having from 1 to 20, and more preferably from 1 to 12, carbon atoms; as hetero atoms, e.g., nitrogen, oxygen, sulfur, and specifically, e.g., imidazolyl, pyridyl, furyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzothiazolyl can be exemplified). These substituents may further be substituted. When there are two or more substituents, they may be the same or different. Substituents may be linked together to form a ring, if possible.
Preferred examples of the substituents include an alkyl group, an alkenyl group, an aralkyl group, an aryl group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, a cyano group, a halogen atom, a hydroxyl group, and a heterocyclic group, more preferred examples include an alkyl group, an alkenyl group, an aralkyl group, an aryl group, an acyl group, an alkoxycarbonyl group, a carbonylamino group, a sulfonylamino group, a cyano group, a halogen atom, and a heterocyclic group, and still more preferred examples include an alkyl group, an aryl group, an alkoxycarbonyl group, a cyano group, and an azole group.
R1 and R3 each preferably represents a hydrogen atom, an alkyl group, an alkoxyl group, an alkoxycarbonyl group, a cyano group, or a condensed ring formed by the linkage of R1 with R2, or R3 with R4, and more preferably a methyl group or a hydrogen atom.
R2 and R4 each preferably represents a hydrogen atom, an alkyl group, or a condensed ring formed by the linkage of R2 with R1, R4 with R3, R2 with R5, or R4 with R6, more preferably a hydrogen atom, a methyl group, or a condensed ring formed by the linkage of R2 with R5, or R4 with R6, and still more preferably a hydrogen atom or a 6-membered ring formed by the linkage of R2 with R5, or R4 with R6, via an alkylene group.
R5 and R6 each preferably represents a hydrogen atom, an alkyl group, an alkylene group, or an aryl group, more preferably an alkyl group, an alkylene group, or an aryl group, still more preferably a methyl group, an ethyl group, or a 6-membered ring formed by the linkage of R5 with R2, or R6 with R4, via an alkylene group, and particularly preferably a methyl group or a 6-membered ring formed by the linkage of R5 with R2, or R6 with R4, via an alkylene group.
R7 preferably represents a hydrogen atom, an alkyl group, an aryl group, a halogen atom, or a cyano group, more preferably a hydrogen atom or an alkyl group, and still more preferably a hydrogen atom.
R8 preferably represents a hydrogen atom, an alkyl group, an aryl group, a halogen atom, a cyano group, or a ring formed by linking with R9, more preferably a hydrogen atom or an alkyl group, and still more preferably a hydrogen atom.
R9 preferably represents a hydrogen atom, an alkyl group, an aryl group, a ring formed by linking with R8, or 
(wherein R1, R2, R3, R4, R5, R6, L1, L2, and n each has the same meaning as in formula (II)), more preferably an alkyl group (preferably an alkyl group having from 2 to 20 carbon atoms, more preferably a branched or cyclic alkyl group having from 3 to 20 carbon atoms, still more preferably a branched or cyclic alkyl group having from 4 to 12 quaternary carbon atoms, and particularly preferably a tert-butyl group), an aryl group (preferably an aryl group having from 6 to 30 carbon atoms and substituted at the opposition, more preferably a phenyl group having from 6 to 30 carbon atoms and substituted with an alkyl group at the o-position, and still more preferably a 2,6-dimethyl-substituted phenyl group), or 
still more preferably an alkyl group (preferably an alkyl group having from 2 to 20 carbon atoms, more preferably a branched alkyl group having from 3 to 20 carbon atoms, still more preferably a branched alkyl group having from 4 to 12 quaternary carbon atoms, and particularly preferably a tert-butyl group), an aryl group (preferably an aryl group having from 6 to 30 carbon atoms and substituted at the o-position, more preferably a phenyl group having from 6 to 30 carbon atoms and substituted with an alkyl group at the o-position, still more preferably a 2,6-dimethyl-substituted phenyl group, and particularly preferably a 2,4,6-trimethylphenyl group), and R9 particularly preferably represents a tert-butyl group or a 2,4,6-trimethylphenyl group, and most preferably a tert-butyl group.
X represents an oxygen atom, a sulfur atom, or Nxe2x80x94R10, wherein R10 represents a hydrogen atom or a substituent. Examples of the substituents represented by R10 include, for example, an alkyl group (preferably an alkyl group having from 1 to 20, more preferably from 1 to 12, and particularly preferably from 1 to 8, carbon atoms, e.g., methyl, ethyl, isopropyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl), an alkenyl group (preferably an alkenyl group having from 2 to 20, more preferably from 2 to 12, and particularly preferably from 2 to 8, carbon atoms,e.g., vinyl, allyl, 2-butenyl, 3-pentenyl), an alkynyl group (preferably an alkynyl group having from 2 to 20, more preferably from 2 to 12, and particularly preferably from 2 to 8, carbon atoms, e.g., propargyl, 3-pentynyl), an aryl group (preferably an aryl group having from 6 to 30, more preferably from 6 to 20, and particularly preferably from 6 to 12, carbon atoms, e.g., phenyl, p-methylphenyl, naphthyl), an acyl group (preferably an acyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., acetyl, benzoyl, formyl, pivaloyl), an alkoxycarbonyl group (preferably an alkoxycarbonyl group having from 2 to 20, more preferably from 2 to 16, and particularly preferably from 2 to 12, carbon atoms, e.g., methoxycarbonyl, ethoxycarbonyl), an aryloxycarbonyl group (preferably an aryloxycarbonyl group having from 7 to 20, more preferably from 7 to 16, and particularly preferably from 7 to 10, carbon atoms, e.g., phenyloxycarbonyl), a sulfamoyl group (preferably a sulfamoyl group having from 0 to 20, more preferably from 0 to 16, and particularly preferably from 0 to 12, carbon atoms, e.g., sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl), a carbamoyl group (preferably a carbamoyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl), a sulfonyl group (preferably a sulfonyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., mesyl, tosyl), a sulfinyl group (preferably a sulfinyl group having from 1 to 20, more preferably from 1 to 16, and particularly preferably from 1 to 12, carbon atoms, e.g., methanesulfinyl, benzenesulfinyl), and a heterocyclic group (preferably a heterocyclic group having from 1 to 20, and more preferably from 1 to 12, carbon atoms; as hetero atoms, e.g., nitrogen, oxygen, sulfur, and specifically, e.g., imidazolyl, pyridyl, furyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzothiazolyl can be exemplified). These substituents may further be substituted. When there are two or more substituents, they may be the same or different. Substituents may be linked together to form a ring, if possible.
Preferred examples of the substituents represented by R10 include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, and a heterocyclic group, more preferred are an alkyl group, an aryl group, and an aromatic heterocyclic group, and still more preferred examples are an alkyl group and an aryl group.
X preferably represents an oxygen atom or Nxe2x80x94R10, and more preferably an oxygen atom.
Z1 represents an atomic group necessary for forming a 5- or 6-membered ring. Specific examples of the 5- or 6-membered rings formed by Z1 include the following:
(a) A 1,3-dicarbonyl nucleus: e.g., 1,3-cyclopentanedione, 1,3-indanedione, 1,3-cyclohexanedione, 5,5-dimethyl-1,3-cyclohexanedione, 1,3-dioxane-4,6-dione, etc.
(b) A pyrazolinone nucleus: e.g., 1-phenyl-2-pyrazolin-5-one, 3-methyl-1-phenyl-2-pyrazolin-5-one, 1-(2-benzothiazolyl)-3-methyl-2-pyrazolin-5-one, etc.
(c) An isooxazolinone nucleus: e.g., 3-phenyl-2-isooxazolin-5-one, 3-methyl-2-isooxazolin-5-one, etc.
(d) An oxyindole nucleus: e.g., 1-alkyl-2,3-dihydro-2-oxyindole, etc.
(e) A 2,4,6-triketohexahydropyrimidine nucleus: e.g., barbituric acid or 2-thiobarbituric acid and derivatives thereof, and as derivatives, e.g., 1-alkyl form such as 1-methyl, 1-ethyl; 1,3-dialkyl form such as 1,3-dimethyl, 1,3-diethyl, 1,3-dibutyl; 1,3-diaryl form such as 1,3-diphenyl, 1,3-di(p-chlorophenyl), 1,3-di(p-ethoxycarbonylphenyl); 1-alkyl-1-aryl form such as 1-ethyl-3-phenyl; and 1,3-di-heterocyclic ring substitution product such as 1,3-di(2-pyridyl) can be exemplified.
(f) A 2-thio-2,4-thiazolidinedione nucleus: e.g., rhodanine and derivatives thereof, and as derivatives, e.g., 3-alkylrhodanine such as 3-methylrhodanine, 3-ethylrhodanine, 3-allylrhodanine; 3-arylrhodanine such as 3-phenylrhodanine; and 3-heterocyclic ring substituted rhodanine such as 3-(2-pyridyl)rhodanine can be exemplified.
(g) A 2-thio-2,4-oxazolidinedione (2-thio-2,4-(3H,5H)-oxazoledione) nucleus: e.g., 3-ethyl-2-thio-2,4-oxazolidinedione, etc.
(h) A thianaphthenone nucleus: e.g., 3-(2H)-thianaphthenone-1,1-dioxide, etc.
(i) A 2-thio-2,5-thiazolidinedione nucleus: e.g., 3-ethyl-2-thio-2,5-thiazolidinedione, etc.
(j) A 2,4-thiazolidinedione nucleus: e.g., 2,4-thiazolidinedione, 3-ethyl-2,4-thiazolidinedione, 3-phenyl-2,4-thiazolidinedione, etc.
(k) A thiazolin-4-one nucleus: e.g., 4-thiazolinone, 2-ethyl-4-thiazolinone, etc.
(l) A 4-thiazolidinone nucleus: e.g., 2-ethylmercapto-5-thiazolin-4-one, 2-alkylphenylamino-5-thiazolin-4-one, etc.
(m) A 2,4-imidazolidinedione (hydantoin) nucleus: e.g., 2,4-imidazolidinedione, 3-ethyl-2,4-imidazolidinedione, etc.
(n) A 2-thio-2,4-imidazolidinedione (2-thiohydantoin) nucleus: e.g., 2-thio-2,4-imidazolidinedione, 3-ethyl-2-thio-2,4-imidazolidinedione, etc.
(o) An imidazolin-5-one nucleus: e.g., 2-propylmercapto-2-imidazolin-5-one, etc.
(p) A 3,5-pyrazolidinedione nucleus: e.g., 1,2-diphenyl-3,5-pyrazolidinedione, 1,2-dimethyl-3,5-pyrazolidinedione, etc.
Preferred examples of the rings formed by Z1 include a 1,3-dicarbonyl nucleus, a pyrazolinone nucleus, a 2,4,6-triketohexahydropyrimidine nucleus (including a thioketone form), a 2-thio-2,4-thiazolidinedione nucleus, a 2-thio-2,4-oxazolidinedione nucleus, a 2-thio-2,5-thiazolidinedione nucleus, a 2,4-thiazolidinedione nucleus, a 2,4-imidazolidinedione nucleus, a 2-thio-2,4-imidazolidinedione nucleus, a 2-imidazolin-5-one nucleus, and a 3,5-pyrazolidinedione nucleus, more preferred are a 1,3-dicarbonyl nucleus, a 2,4,6-triketohexahydropyrimidine nucleus (including a thioketone form), and a 3,5-pyrazolidinedione nucleus, still more preferred are a cyclic 1,3-dicarbonyl nucleus, a barbituric acid derivative, a 2-thiobarbituric acid derivative, and a 3,5-pyrazolidinedione nucleus, and particularly preferred are 1,3-indanedione and 1,2-diphenyl-3,5-pyrazolidinedione.
L1 and L2 each represents a substituted or unsubstituted methine group. L1 and L2 may respectively form 4- to 6-membered rings via the substituent of the substituted methine group, or L1 and L2 may be linked to each other to form a 4- to 6-membered ring.
As the substituents of the substituted methine group, e.g., those exemplified as the substituents for R1 to R9 can be applied, preferably an alkyl group, an aryl group, an aralkyl group, an alkoxyl group, an aryloxy group, an alkylthio group, an arylthio group, a cyano group, or a halogen atom, more preferably an alkyl group or an alkoxyl group, and still more preferably a lower alkyl group (preferably having from 1 to 4 carbon atoms).
L1 and L2 each preferably represents an unsubstituted methine group, an alkyl-substituted methine group, or an alkoxyl-substituted methine group, and more preferably an unsubstituted methine group.
n represents 1 or 2, preferably 1.
The compound represented by formula (II) is preferably represented by formula (III): 
wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, L1, L2 and n each has the same meaning as defined in formula (II), and the preferred range is also the same. Z2 represents an atomic group necessary for forming a 5- or 6-membered ring, as the 5- or 6-membered rings formed by Z2, e.g., among the rings formed by Z1 in formula (II), those having 1,3-dicarbonyl structure in the ring, e.g., 1,3-cyclopentanedione, 1,3-cyclohexanedione, 1,3-indanedione, and 3,5-pyrazolidinedione can be exemplified, and preferred are 1,3-indanedione and 1,2-diphenyl-3,5-pyrazolidinedione.
The compound represented by formula (II) is more preferably represented by formula (IV) or (V): 
wherein R1, R2, R3, R4, R5, R6, R7, R8, L1, L2, Z2 and n each has the same meaning as formula (III), and the preferred range is also the same. R31 represents an alkyl group having 2 or more carbon atoms (preferably an alkyl group having from 2 to 20 carbon atoms, more preferably a branched or cyclic alkyl group having from 3 to 20 carbon atoms, still more preferably a branched or cyclic alkyl group having from 4 to 12 quaternary carbon atoms, and particularly preferably a tert-butyl group), or an aryl group (preferably an aryl group having from 6 to 30 carbon atoms and substituted at the o-position, and still more preferably an o-alkyl-substituted phenyl group (e.g., a 2,6-dimethylphenyl group, a 2,4,6-trimethylphenyl group), and particularly preferably a 2,4,6-trimethylphenyl group).
When R7 and R8 both represent a hydrogen atom, R31 more preferably represents a tert-butyl group, a 2,6-dimethylphenyl group or a 2,4,6-trimethylphenyl group, and still more preferably represents a tert-butyl group. 
wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, L1, L2 and n each has the same meaning as defined in formula (II), and the preferred range is also the same. As the substituents represented by R51 and R52, e.g., those exemplified as the substituents for R1 to R9 in formula (II) can be applied, preferably a hydrogen atom, an alkyl group (preferably an alkyl group having from 1 to 20, more preferably from 1 to 12, and still more preferably from 1 to 8, carbon atoms), an aryl group (preferably an aryl group having from 6 to 30, more preferably from 6 to 20, and still more preferably from 6 to 12, carbon atoms), or a heterocyclic group, more preferably an alkyl group, an aryl group, or a heterocyclic group, still more preferably a methyl group, an ethyl group, or a substituted or unsubstituted phenyl group, particularly preferably a methyl group or a substituted or unsubstituted phenyl group, and most preferably a phenyl group. R51 and R52 may be linked together to form a ring, if possible.
The compound represented by formula (IV) is more preferably represented by formula (IV-a): 
wherein R1, R2, R3, R4, R5, R6, R7, R8, L1, L2 and n each has the same meaning as defined in formula (II), and the preferred range is also the same. R31 has the same meaning as defined in formula (IV) and the preferred range is also the same. As the substituents represented by R41, R42, R43 and R44, e.g., those exemplified as the substituents for R1 to R9 in formula (II) can be applied. R41 to R44 may be linked together to form a ring, if possible. R41 to R44 each preferably represents a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, a halogen atom, a cyano group, an alkoxyl group, an aryloxy group, an alkoxycarbonyl group, or an aryloxycarbonyl group, more preferably a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, a halogen atom, or a cyano group, and particularly preferably a hydrogen atom.
The compound represented by formula (II) may be a low molecular weight compound, may be a high molecular weight compound the polymer main chain of which is connected with the residue represented by formula (II) (preferably having a weight average molecular weight of from 1,000 to 5,000,000, more preferably from 5,000 to 2,000,000, and still more preferably from 10,000 to 1,000,000), or may be a high molecular weight compound whose main chain has the skeleton of formula (II) (preferably having a weight average molecular weight of from 1,000 to 5,000,000, more preferably from 5,000 to 2,000,000, and still more preferably from 10,000 to 1,000,000). The high molecular weight compound may be a homopolymer or a copolymer with other monomers.
The compound represented by formula (II) is preferably a low molecular weight compound. Further, formula (II) is conveniently represented as an extreme structural formula but the compound may be a tautomer. When there exists a geometrical isomer, the compound may be either one.
Specific examples of the compound represented by formula (II) are shown below but the present invention is not limited thereto. 
Weight average molecular weight (12,000, calculated in terms of polystyrene)
x/y=1/100 (by weight) 
The above-described compounds may be tautomers thereof.
Synthesis methods of the compounds according to the present invention will be described below. Representative synthesis methods are shown in Schemes 1 to 3 below.

wherein R9 has the same meaning as defined in Formula (II).
In Scheme 1, the synthesis of (A) to (B) is a synthesis method using ketone compound (A) and an acid anhydride in the presence of a boron trifluoride complex (see Zeitschrift Chemie, Vol. 28, p. 23 (1988)), the synthesis of (B) to (D) is a method using (B) and acetal compound (C) in the presence of a base, and the synthesis of (D) to (E) is a synthesis method based on the method of cyclization under the acidic conditions.

wherein R51 and R52 each has the same meaning as defined in formula (V).
In Scheme 2, the synthesis of (F) to (H) is a synthesis method based on the method of amidation of hydrazine derivative (F) and malonic acid derivative (G) in the presence of a base, and the synthesis can be performed according to the method described in J. Gen. Chem. USSR, Vol. 28, p. 2841 (1958).

wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, L1, L2, Z1 and n each has the same meaning as defined in formula (II), L3 and L4 each represents a substituted or unsubstituted methine group, and m represents 0 or 1.
In Scheme 3, the synthesis of (E) to (L) is a synthesis method based on a dehydration condensation reaction using acid anhydrides R8 and R9 to ketone compound (I) and intermediate (E) (see J. Amer. Chem. Soc., Vol. 80, p. 1440 (1958). The synthesis of (J) to (L) is a synthesis method based on the Knoevenagl reaction of subjecting activated methylene and aldehyde to a dehydration condensation reaction in the presence of a base (see JP-A-60-83035) (the term xe2x80x9cJP-Axe2x80x9d as used herein means an xe2x80x9cunexamined published Japanese patent applicationxe2x80x9d).